Sodium hydride → 6-(2-(Ethylamino)-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl pivalate

HRID 1433926Notes

Reaction equation

HRID 1433926 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH:12]1[CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([OH:22])[CH:16]=[CH:15][C:14]=2[CH2:13]1)[CH3:2].[H-].[Na+].[CH3:25][C:26]([CH3:36])([CH3:35])[C:27](N1CCSC1=S)=[O:28].[Cl-].[NH4+]>O1CCCC1>[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH:12]1[CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([O:22][C:27](=[O:28])[C:26]([CH3:36])([CH3:35])[CH3:25])[CH:16]=[CH:15][C:14]=2[CH2:13]1)[CH3:2]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 117695952,2-Dimethyl-1-(2-thioxothiazolidin-3-yl)propan-1-oneHCID 230874442-Naphthalenol, 6-[2-(ethylamino)-4-methoxyphenyl]-5,6,7,8-tetrahydro-

Product 1

HCID 579340956-(2-(Ethylamino)-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl pivalateYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-(2-ethylamino-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol (500 mg) in tetrahydrofuran (15 ml) was added 60% sodium hydride (75 mg) under a nitrogen atmosphere, the solution was stirred for 30 minutes at room temperature, then 2,2-dimethyl-1-(2-thioxothiazolidin-3-yl)propan-1-one (380 mg) was added thereto on an ice bath followed by stirring for 25 minutes. A saturated aqueous solution of ammonium chloride was added thereto, the solution was stirred, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (640 mg).

Workup

  1. customon an ice bath followed
  2. stirringby stirring for 25 minutes
  3. stirringthe solution was stirred
  4. extractionextracted with ethyl acetate
  5. washsequentially washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-2e5b34992e4e446daf3beb1651a0289a
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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